Holiday Rentals in Cayman Islands

2552 available vacation rental offers

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Cayman Islands holiday rentals
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Cayman Islands holiday rentals: compare the best deals

Best family friendly Cayman Islands holiday rentals

Among the 2552 accommodations in Cayman Islands, here are the 4 best family friendly rentals

Wyndham Reef Resort, Grand Cayman - Cayman Islands
8.5 1705 reviews
Cayman Islands
07/18 – 08/01
HK$1616/nighttotal: HK$22624 (14 )

Wyndham Reef Resort, Grand Cayman

1 2
resort , Sand Bluff
The Wyndham Reef Resort is situated on the East End of Grand Cayman, just a short drive from the East End Marshland, Queen Elizabeth II Botanic Park, and Rum Point. The resort has consistently received very good ratings for its location, user experience, and cleanliness, ensuring a pleasant stay.
The resort offers a range of studios and apartments, all featuring air conditioning, kitchenettes, and private terraces with stunning sea views. Guests can enjoy a variety of activities, including swimming, tennis, yoga, and spa treatments, as well as dining at the resort's two restaurants and bar.
Tamarind Bay Unit # 22 - Cayman Islands
9.0 1 review
Cayman Islands
01/11 – 04/05
HK$7482/nighttotal: HK$628488 (84 )

Tamarind Bay Unit # 22

3 2
apartment , Seven Mile Beach
Tamarind Bay Unit #22 is a three-bedroom apartment directly on Seven Mile Beach, Grand Cayman, 5 km from Owen Roberts International Airport.
This beachfront property sleeps 11, boasts a fully equipped kitchen, private parking, swimming pool, tennis court, concierge service, and offers easy access to snorkelling and fishing.
Beach & Pool In 2br Secluded Condo At Rum Point - Cayman Islands
10 44 reviews
Cayman Islands
01/11 – 04/05
HK$2527/nighttotal: HK$212268 (84 )

Beach & Pool In 2br Secluded Condo At Rum Point

2 2
apartment , Rum Point
This ground floor apartment is situated just 5km from Rum Point and 8km from Crystal Cavern, in a quiet area of North Side, offering a secluded escape from the hustle and bustle of Grand Cayman. The property has received excellent ratings for user experience, location, and cleanliness.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It boasts a fully equipped kitchen, air conditioning, a swimming pool, a garden, and direct access to a semi-private beach, offering everything you need for a relaxing and enjoyable stay.
Moon Bay # 5 - Cayman Islands
9.7 4 reviews
Cayman Islands
10/01 – 10/08
HK$1950/nighttotal: HK$13650 (7 )

Moon Bay # 5

2 2
apartment , Bodden Town
Moon Bay #5 apartment in Bodden Town, Grand Cayman, is situated 15 kilometres from Owen Roberts International Airport, offering easy access to the island's main airport.
This self-catering flat boasts a 98 square metre, air-conditioned one-bedroom layout with a private garden, balcony, swimming pool, and sleeps one guest, perfect for a peaceful retreat.

Best Cayman Islands holiday rentals with a pool

Among the 2552 accommodations in Cayman Islands, here are the 4 best rentals with a pool

Serene Home With Saltwater Pool & Gardens - Cayman Islands
10 25 reviews
Cayman Islands
06/27 – 07/04
HK$2874/nighttotal: HK$20118 (7 )

Serene Home With Saltwater Pool & Gardens

1 2
apartment , Savannah
This Savannah apartment boasts three bedrooms, three bathrooms, and sleeps six, offering easy access to Savannah's attractions.
The property features a saltwater pool, expansive patio, fully equipped kitchen with laundry facilities, a versatile gym/office, and is ideally located for exploring nearby beaches and restaurants.
Scuba & Family Home - Sleeps 9 - Dreamcayman - Cayman Islands
10 3 reviews
Cayman Islands
07/20 – 07/29
HK$3372/nighttotal: HK$30348 (9 )

Scuba & Family Home - Sleeps 9 - Dreamcayman

1 6
apartment , West Bay
This three-bedroom, three-bathroom townhouse in West Bay, Grand Cayman, enjoys direct access to a world-class shore diving site and is situated near the Macabuca restaurant and dive centre.
The spacious property, sleeping up to nine guests across three floors, boasts a fully equipped kitchen, patio with BBQ, two swimming pools, a jacuzzi, and private parking; on-site dive facilities are also available.
Luxury 2br Condo | Walk To Seven Mile Beach, Pools - Cayman Islands
9.9 42 reviews
Cayman Islands
10/01 – 10/08
HK$2187/nighttotal: HK$15309 (7 )

Luxury 2br Condo | Walk To Seven Mile Beach, Pools

1 2
apartment , George Town
This George Town apartment, situated within a gated community near Seven Mile Beach, offers convenient access to George Town's attractions.
The two-bedroom, one-bathroom flat sleeps four guests, boasting a king and queen-size bed, full kitchen, in-unit laundry, private balcony with pool and canal views, and access to three pools, a hot tub, gym, and clubhouse.
Beautiful Modern Condo On 7 Mile Beach - Cayman Islands
9.7 190 reviews
Cayman Islands
10/01 – 10/05
HK$2956/nighttotal: HK$11824 (4 )

Beautiful Modern Condo On 7 Mile Beach

1 4
apartment , George Town
This two-bedroom apartment is situated on the famous Seven Mile Beach, just a short distance from George Town, offering stunning views and easy access to the area's best attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious and comfortably sleeps up to six guests. It features a fully equipped kitchen with modern appliances, air conditioning throughout, and a private balcony with views of the ocean. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, and access to the nearby Margaritaville Resort.

Frequently asked questions about holiday rentals in Cayman Islands

  • What are the must-see places in the Cayman Islands?

    Seven Mile Beach is a must, of course. Stingray City is iconic for its shallow-water encounters. For a bit of history, explore the Pedro St James National Historic Site. And don't miss the beautiful scenery at the Queen Elizabeth II Botanic Park.
  • What are the best Airbnb and vacation rentals in Cayman Islands?

    Regal Beach Club #114, Cayman Reef Resort 33 - Anchors Away and Mar 20-24 Avail Cayman Reef 47 King Bed 65" Tv - Bright Airy Fully Stocked are the most popular Airbnb and vacation rentals in Cayman Islands among travelers.

  • What are the typical activities to do in the Cayman Islands?

    Snorkelling and diving are hugely popular, especially around the reefs. Stingray City is a top choice for a unique experience. You can also enjoy watersports like jet skiing and paddleboarding. Relaxing on the beaches is another favourite, of course.
  • What are the most popular Airbnbs in Cayman Islands?

  • Which part of the Cayman Islands offers the most pleasant climate?

    The climate is generally pleasant across the islands, but Grand Cayman tends to be slightly more consistent. The smaller islands, Cayman Brac and Little Cayman, can experience more variation in wind and temperature.
  • What are the best vacation rentals with a pool in Cayman Islands?

  • What airport options are there for reaching the Cayman Islands?

    Owen Roberts International Airport (GCM) on Grand Cayman is the main airport. There are smaller airstrips on Cayman Brac and Little Cayman, but most international flights arrive at GCM.
  • What are the best rentals for families and kids in Cayman Islands?

  • Are there specific challenges to driving in the Cayman Islands that visitors should know?

    Driving is on the left-hand side of the road, which can take some getting used to. Roads can be narrow in places, especially outside of the main towns. Be aware of the speed limits, and always drive cautiously.
  • What are the best rentals or Airbnbs with a jacuzzi in Cayman Islands?

  • What currency is used in the Cayman Islands?

    The Cayman Islands dollar (KYD) is the official currency, but US dollars are widely accepted.
  • What are the top festivals to experience in the Cayman Islands?

    The Pirates Week Festival is a big one, celebrating the islands' maritime history with parades, and cultural events. The annual Batabano Carnival is also popular, known for its vibrant costumes and street parade.
  • What is the best time of year to visit the Cayman Islands?

    The best time to visit is during the dry season, from November to April, when the weather is sunny and warm, and the humidity is lower. Hurricane season is from June to November.
  • What are some local dishes to try in the Cayman Islands?

    Conch is a staple, often served in fritters, ceviche or in a stew. Try the Cayman-style jerk chicken or fish, and don't miss the local seafood dishes featuring fresh wahoo or snapper.
  • What emergency numbers should you know in case of a medical or security issue in the Cayman Islands?

    For medical emergencies, dial 911. For police, also dial 911.
  • What etiquette tips are important when visiting the Cayman Islands?

    Being polite and respectful is always appreciated. Remember that the islands are a relaxed place, so casual attire is generally fine. Tipping is customary in restaurants and for service providers.
  • What are the best areas to spend a week in the Cayman Islands?

    Seven Mile Beach offers a range of luxury resorts and is perfect for those seeking a relaxing beach holiday. For a more secluded experience, consider Little Cayman or Cayman Brac.
  • What are the best areas to spend a weekend in the Cayman Islands?

    Grand Cayman's Seven Mile Beach area is ideal for a short break, offering easy access to beaches, restaurants and activities. George Town offers a more urban experience.
  • What are the top shopping destinations in the Cayman Islands?

    Camana Bay offers a mix of high-end boutiques and local shops. George Town has a variety of duty-free shops.
  • What are some off-the-beaten-path places to explore in the Cayman Islands?

    The Bluff in Little Cayman offers stunning views and secluded beaches. Explore the caves and blow holes on Cayman Brac for a unique experience.

Best Cayman Islands holiday rentals with parking

Northern Lights #4 Condo - Cayman Islands
9.0 2 reviews
Cayman Islands
07/21 – 07/28
HK$2734/nighttotal: HK$19138 (7 )

Northern Lights #4 Condo

1 2
house , Old Man Bay
Northern Lights #4 Condo is a beachfront property in Old Man Bay, Grand Cayman, situated steps from Old Man Bay Beach and 27 kilometres from Owen Roberts International Airport.
This two-bedroom, two-bathroom beachfront apartment offers 172 square metres of living space, sleeping up to nine guests and boasting a fully equipped kitchen, free Wi-Fi, and private parking.
South Bay #7- 2 Bedroom 2 Bathroom Unit - Cayman Islands
10 1 review
Cayman Islands
06/27 – 07/04
HK$4553/nighttotal: HK$31871 (7 )

South Bay #7- 2 Bedroom 2 Bathroom Unit

1 2
apartment , Seven Mile Beach
This two-bedroom, two-bathroom apartment in Dog City, Grand Cayman, is situated a short distance from Seven Mile Beach and 5km from Owen Roberts International Airport.
The self-catering flat offers free Wi-Fi, air conditioning, a private patio, swimming pool access, and parking (subject to availability), sleeping up to seven guests.
South Bay Beach Club #6 - 2 Bedroom 2 Bathroom Unit - Cayman Islands
Cayman Islands
06/27 – 07/04
HK$3934/nighttotal: HK$27538 (7 )

South Bay Beach Club #6 - 2 Bedroom 2 Bathroom Unit

2 2
apartment , George Town
This beachfront apartment in George Town, Grand Cayman, is situated a short walk from Seven Mile Beach and 5 kilometres from Owen Roberts International Airport.
The 126 square metre flat offers two bedrooms, two bathrooms, and sleeps up to seven guests, boasting a fully equipped kitchen, air conditioning, a swimming pool, garden, parking, and free Wi-Fi.
Colonial Kai Condo - Cayman Islands
10 1 review
Cayman Islands
11/28 – 12/05
HK$2880/nighttotal: HK$20160 (7 )

Colonial Kai Condo

1 3
house , Driftwood Village
Colonial Kai Condo, a two-bedroom house in Driftwood Village, is a 3-minute walk from Water Cay Public Beach and 2.4 kilometres from Rum Point Beach.
This 116-square-metre property sleeps seven, boasting two bathrooms, a fully equipped kitchen with dishwasher, a Jacuzzi, free Wi-Fi, private parking, and bed linen and towels provided; no stag or hen parties are permitted.

Best Cayman Islands holiday rentals with a balcony

Aqua Bay Premium 7mile Beach Family Unit - Cayman Islands
Cayman Islands
10/01 – 10/05
HK$4680/nighttotal: HK$18720 (4 )

Aqua Bay Premium 7mile Beach Family Unit

1 4
apartment , West Bay
This West Bay flat offers a prime location just a few steps from the renowned Seven Mile Beach, situated 9.9 kilometres from Owen Roberts International Airport.
This 130 square metre apartment accommodates up to 11 guests, featuring air conditioning, a dishwasher, a terrace, a balcony, and communal access to a swimming pool and hot tub.
Featherstone Estate, Cayman Brac - Cayman Islands
Cayman Islands
06/27 – 07/04
HK$10725/nighttotal: HK$75075 (7 )

Featherstone Estate, Cayman Brac

4 2
house , Cayman Brac
This beachfront Cayman Brac villa, situated in the Featherstone Estate, is 12 kilometres from Charles Kirkconnell International Airport.
The 265 square metre property offers four bedrooms, four bathrooms, three living rooms, accommodating up to 21 guests, and features a private pool, extensive outdoor space with barbecue facilities, and easy access to snorkelling, cycling, and fishing.
Casa Luna 16 - Cayman Islands
10 1 review
Cayman Islands
07/21 – 07/28
HK$10663/nighttotal: HK$74641 (7 )

Casa Luna 16

1 2
house , George Town
This George Town apartment, a 4km drive from Owen Roberts International Airport, offers stunning sea views.
Sleeping up to 10 guests, the three-bedroom, four-bathroom property boasts a fully equipped kitchen with dishwasher and microwave, air conditioning, private parking, a swimming pool, terrace, and complimentary Wi-Fi.
Modern 1 Bedroom Walking Distance To The Beach! - Cayman Islands
Cayman Islands
08/27 – 09/07
HK$1325/nighttotal: HK$14575 (11 )

Modern 1 Bedroom Walking Distance To The Beach!

1 1
apartment , West Bay
This West Bay apartment, a two-minute walk from Seven Mile Beach and 11km from Owen Roberts International Airport, offers convenient access to Grand Cayman's renowned beach and airport.
The 60-square-metre flat boasts one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, free Wi-Fi, private parking, a swimming pool, and a terrace.
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